Montegrossi Holiday Rentals, Gaiole in Chianti: Private House Rentals

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Hot tub

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Farm

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Our top choices for Montegrossi hotels

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

1. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Rama

฿13,159

฿14,858 total

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

A modern living room with a white sofa, armchairs, and a coffee table.

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

2. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

฿9,181

฿10,329 total

includes taxes & fees

7 Oct - 8 Oct

A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.

A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.

A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.

3. Borgo Vescine

Radda in Chianti

Gabrielle

฿30,078

฿33,392 total

includes taxes & fees

11 Sept - 12 Sept

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

A room with a view of a forest through a window, a table with a lamp, and a chair.

4. Dievole Wine Resort

Castelnuovo Berardenga

Karamjit

฿12,000

฿13,506 total

includes taxes & fees

11 Oct - 12 Oct

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

5. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

฿4,532

฿5,292 total

includes taxes & fees

30 Sept - 1 Oct

A spa area with a stone ceiling, a pool, and two sun loungers.

A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.

A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.

A buffet area with various fruits and a bar with bottles.

6. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

฿6,563

฿7,449 total

includes taxes & fees

5 Oct - 6 Oct

A couple dining at an outdoor table with a view of the countryside.

A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

A narrow street with buildings on either side, a flag, and a bench.

A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

7. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

฿7,645

฿8,639 total

includes taxes & fees

5 Oct - 6 Oct

A large building with multiple rooms, surrounded by a field of lavender.

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

An arched brick corridor leading to a dining area with tables set for a meal.

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

8. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Hannah

฿20,505

฿22,938 total

includes taxes & fees

7 Oct - 8 Oct

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A table set for breakfast with various dishes, drinks, and a newspaper.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

9. Hotel Le Fontanelle

Castelnuovo Berardenga

Briana

฿18,749

฿21,007 total

includes taxes & fees

5 Oct - 6 Oct

A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.

A table set with wine glasses and a candle, viewed through a window with string lights.

A white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.

A building with a brick facade, arched entrance, and multiple windows covered in green ivy.

10. Tenuta CorteDomina

Radda in Chianti

Dustin

฿8,359

฿9,348 total

includes taxes & fees

30 Sept - 1 Oct

An outdoor dining area with a pool, potted plants, and umbrellas.

A villa with a swimming pool, outdoor seating, and a garden.

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

11. Relais Vignale & Spa

Radda in Chianti

Maaya

฿5,904

฿7,670 total

includes taxes & fees

8 Oct - 9 Oct

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

An arched stone structure with a view of a landscaped garden and a building with outdoor seating.

A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

12. The Club House

Castelnuovo Berardenga

Karla

฿29,591

฿32,933 total

includes taxes & fees

27 Sept - 28 Sept

A person pouring a liquid from a bottle into a glass.

A modern building with a glass facade, a car parked in front, and a well-lit entrance area.

A modern interior with a blue chair, a yellow chair, and a brown sofa. There is a glass door leading to an outdoor area with chairs and plants.

A modern interior with a yellow sofa, blue armchair, and a dining area with chairs and a table.

13. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

฿3,881

฿4,384 total

includes taxes & fees

20 Sept - 21 Sept

A historic stone building with multiple windows and a courtyard.

A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

A pool area with lounge chairs and a service person attending to a guest.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

14. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

฿23,707

฿26,461 total

includes taxes & fees

11 Oct - 12 Oct

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.

A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.

15. Hotel Villa Campomaggio

Radda in Chianti

Krishna

฿8,146

฿9,190 total

includes taxes & fees

29 Sept - 30 Sept

A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.

A stone-walled room with a sofa, a coat rack, and a window with curtains.

A rectangular swimming pool with a view of mountains in the background.

A stone house with a tiled roof, surrounded by greenery and a gravel path.

16. Podere L'Aquila

Gaiole in Chianti

฿5,634

฿15,647 total

includes taxes & fees

27 Sept - 28 Sept

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

A stone building with a wooden door, outdoor seating, and a pergola with vines.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

17. Agriturismo San Sano

Gaiole in Chianti

Ernesto

฿2,846

฿3,284 total

includes taxes & fees

11 Oct - 12 Oct

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

18. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

"Ultimo Mulino Hotel was amazing! The property is so peaceful and beautiful. We had breakfast both mornings and ate at their on site restaurant both evenings. The food was delicious and the staff was incredible. Leno was our server both nights- she was amazing and so helpful making suggestions on food and wines. We also enjoyed the spa for the wellness package and a couples massage for our honeymoon. We highly recommend this to everyone! It was so relaxing and worth the cost."

Hannah

฿3,812

฿4,499 total

includes taxes & fees

6 Oct - 7 Oct

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

A building with arched windows, a courtyard with a pond, and a metal fence.

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

19. Hotel Casafrassi

Castellina in Chianti

Jane

฿2,054

฿2,489 total

includes taxes & fees

11 Sept - 12 Sept

A spacious lobby with a reception desk, seating area, and a large vase.

A patio with a round table and chairs, potted plants, and a view of the building's interior.

A hotel room with two beds, a desk with a computer, a chair, and a tray of breakfast items.

A modern hotel lobby with a curved reception desk, seating area, and a bar.

20. Hotel Valdarno

Montevarchi

Emmanuel

฿4,073

฿4,480 total

includes taxes & fees

13 Sept - 14 Sept

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Top Montegrossi Hotel Reviews

Borgo Vescine

10/10 Excellent

"This place is simply perfection From the moment you check in to the moment you leave , you feel like royalty . Staff is impressive how polite , accommodating and welcoming Thank you Lorenzo at the bar ! Honestly no words besides EXCELLENT Anna /Canada !!!!"

Villa Pitiana

10/10 Excellent

"We spent our honeymoon here and it was absolutely beautiful"

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The staff were very friendly and helpful. The bar service is the best."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"All the staff in the hotel were very helpful and we would like to stay there again."

Hotel Chiusarelli

10/10 Excellent

"Great location. Wonderful staff, very helpful and polite."

Hotel Athena

10/10 Excellent

"Clean, well located, friendly staff, wonderful views"

Borgo San Felice Resort

10/10 Excellent

"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"

Fattoria di Vegi

10/10 Excellent

"Amazing! I wish I could have stayed forever!"

Dievole Wine Resort

10/10 Excellent

"Amazing hotel with the most unreal views. Staff were super friendly. Would definitely recommend!"

More cheap stays in Montegrossi

Cannon d'Oro

Via Montanini 28 Siena SI

฿3,178

฿3,687 total

24 Sept - 25 Sept

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

฿4,173

฿4,782 total

15 Sept - 16 Sept

includes taxes & fees

7.8/10 Good! (435 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

฿5,217

฿5,930 total

5 Oct - 6 Oct

includes taxes & fees

8.8/10 Excellent! (106 reviews)

Antico Borgo Poggiarello

Strada Di San Monti 12 Monteriggioni SI

฿5,796

฿6,491 total

11 Oct - 12 Oct

includes taxes & fees

9/10 Wonderful! (20 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

฿5,865

฿6,643 total

11 Oct - 12 Oct

includes taxes & fees

10/10 Exceptional! (49 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

Frequently asked questions

Where is the best place to stay in Montegrossi?

Located 9.1 mi (14.6 km) from the heart of Montegrossi, La Certosa di Pontignano is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Hotel Athena and Grand Hotel Continental Siena – Starhotels Collezione. See all available top hotels, or vacation rentals in Montegrossi.

What are some of the best holiday rentals that Montegrossi has to offer?

Borgo Argiano: This holiday home rental outside of Montegrossi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library. See all vacation rentals in Montegrossi.

If I need to cancel my hotel reservation in Montegrossi, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Montegrossi.

What are some hotels with pools in Montegrossi?

Castello di Spaltenna- Small Luxury Hotels of the World: Offers an indoor pool, an outdoor pool and 2 restaurants. Hotel Borgo di Cortefreda Relais and Four Points by Sheraton Siena are two additional hotels that feature an on-site pool. View all hotels with pools in Montegrossi.

How is it to stay in Montegrossi?

Visitors to Montegrossi will definitely find plenty to explore and enjoy. In Montegrossi, there are 4 hotels and other accommodation options to choose from. Find out more about Montegrossi.

What are the top places to visit in Montegrossi?

Places to visit in the wider area include Badia a Coltibuono, Meleto Castle and Castello di Albola. You'll also find Castello di Radda Winery and Castle of Brolio in the area. Take a look at what more there is to see and do in Expedia's Montegrossi guide.

What's the seasonal weather like in Montegrossi?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Montegrossi is 946 mm.

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Book Hotels in Montegrossi on Expedia.it

Find hotels in Montegrossi from ฿2,489

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montegrossi

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Montegrossi hotels

1. Castello di Spaltenna- Small Luxury Hotels of the World

2. Chapter Chianti, a Member of Design Hotels

3. Borgo Vescine

4. Dievole Wine Resort

5. La Certosa di Pontignano

6. Hotel Palazzo San niccolò & Spa

7. Palazzo Leopoldo Dimora Storica & Spa

8. Borgo Scopeto Wine & Country Relais

9. Hotel Le Fontanelle

10. Tenuta CorteDomina

11. Relais Vignale & Spa

12. The Club House

13. Moody smart & comfy Hotel

14. Borgo San Felice Resort

15. Hotel Villa Campomaggio

16. Podere L'Aquila

17. Agriturismo San Sano

18. Ultimo Mulino Wellness Country Hotel

19. Hotel Casafrassi

20. Hotel Valdarno

Top Montegrossi Hotel Reviews

Borgo Vescine

Villa Pitiana

Villa Scacciapensieri Boutique Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Chiusarelli

Hotel Athena

Borgo San Felice Resort

Fattoria di Vegi

Dievole Wine Resort

More cheap stays in Montegrossi

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Antico Borgo Poggiarello

Torre del Fuggisole

Porta Pispini Residence

Frequently asked questions

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